CH549051A - Verfahren zum reinigen von 7-amino-cephalosporansaeure. - Google Patents
Verfahren zum reinigen von 7-amino-cephalosporansaeure.Info
- Publication number
- CH549051A CH549051A CH745265A CH745265A CH549051A CH 549051 A CH549051 A CH 549051A CH 745265 A CH745265 A CH 745265A CH 745265 A CH745265 A CH 745265A CH 549051 A CH549051 A CH 549051A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- solution
- water
- aca
- salt
- Prior art date
Links
- 238000007670 refining Methods 0.000 title 1
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 claims abstract description 61
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 14
- -1 7-ACA hydrogen Chemical class 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 13
- 239000000725 suspension Substances 0.000 claims description 13
- 239000012535 impurity Substances 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 11
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 8
- 229910017604 nitric acid Inorganic materials 0.000 claims description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- BLUNNZYDUZHPAD-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;dihydrate Chemical compound O.O.CC1=CC=C(S(O)(=O)=O)C=C1 BLUNNZYDUZHPAD-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 238000000746 purification Methods 0.000 abstract 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 44
- 239000007787 solid Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000001914 filtration Methods 0.000 description 15
- 238000003756 stirring Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Chemical class 0.000 description 5
- 238000006073 displacement reaction Methods 0.000 description 5
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 229940113088 dimethylacetamide Drugs 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N Cephalosporin C Natural products S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- HOKIDJSKDBPKTQ-GLXFQSAKSA-M cephalosporin C(1-) Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- AJYXPNIENRLELY-UHFFFAOYSA-N 2-thiophen-2-ylacetyl chloride Chemical compound ClC(=O)CC1=CC=CS1 AJYXPNIENRLELY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004157 Nitrosyl chloride Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000005947 deacylation reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 2
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 2
- 235000019392 nitrosyl chloride Nutrition 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical group SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
-
- E—FIXED CONSTRUCTIONS
- E02—HYDRAULIC ENGINEERING; FOUNDATIONS; SOIL SHIFTING
- E02F—DREDGING; SOIL-SHIFTING
- E02F7/00—Equipment for conveying or separating excavated material
- E02F7/10—Pipelines for conveying excavated materials
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Mining & Mineral Resources (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Structural Engineering (AREA)
- Medicinal Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Civil Engineering (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB22155/64A GB1104938A (en) | 1964-05-28 | 1964-05-28 | Improvements in or relating to 7-aminocephalosporanic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH549051A true CH549051A (de) | 1974-05-15 |
Family
ID=26255771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH745265A CH549051A (de) | 1964-05-28 | 1965-05-28 | Verfahren zum reinigen von 7-amino-cephalosporansaeure. |
Country Status (12)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3824238A (en) * | 1972-04-05 | 1974-07-16 | Squibb & Sons Inc | Method for the purification of 7-amino-desacetoxycephalosporanic acid |
| JPS5113988U (enrdf_load_stackoverflow) * | 1974-07-13 | 1976-01-31 | ||
| US4754030A (en) * | 1985-02-01 | 1988-06-28 | Bristol-Myers Company | Cefbuperazone crystalline triethylamine salt |
| US6518420B2 (en) * | 1997-06-04 | 2003-02-11 | Biochemie Gesellschaft M.B.H. | Precipitation process of 7-aminocephalosporanic acid (7-ACA) |
| SK165399A3 (en) * | 1997-06-04 | 2000-05-16 | Biochemie Gmbh | Process for the preparation of rosettes or agglomerates of 7-aminocephalosporanic acid (7-aca) |
| FR2866942B1 (fr) | 2004-03-01 | 2006-04-14 | Inst Francais Du Petrole | Connecteur pour colonne montante haute pression |
| CN102321099A (zh) * | 2011-08-15 | 2012-01-18 | 华北制药河北华民药业有限责任公司 | 一种头孢烷酸的结晶方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB953695A (en) * | 1959-08-04 | 1964-03-25 | Nat Res Dev | Derivatives of cephalosporin c |
| US3216999A (en) * | 1961-08-23 | 1965-11-09 | Lilly Co Eli | Carbocyclic cephalosporins |
-
1964
- 1964-05-28 GB GB22155/64A patent/GB1104938A/en not_active Expired
-
1965
- 1965-05-24 IL IL23589A patent/IL23589A/en unknown
- 1965-05-24 US US458446A patent/US3507860A/en not_active Expired - Lifetime
- 1965-05-28 AT AT488765A patent/AT266315B/de active
- 1965-05-28 FR FR18642A patent/FR1457319A/fr not_active Expired
- 1965-05-28 BE BE664646D patent/BE664646A/xx not_active IP Right Cessation
- 1965-05-28 DE DE19651795694 patent/DE1795694A1/de active Pending
- 1965-05-28 DE DE1545898A patent/DE1545898C3/de not_active Expired
- 1965-05-28 DK DK270065AA patent/DK137191B/da unknown
- 1965-05-28 NL NL656506820A patent/NL144281B/xx not_active IP Right Cessation
- 1965-05-28 JP JP40031152A patent/JPS499475B1/ja active Pending
- 1965-05-28 SE SE7039/65A patent/SE317079B/xx unknown
- 1965-05-28 CH CH745265A patent/CH549051A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE317079B (enrdf_load_stackoverflow) | 1969-11-10 |
| GB1104938A (en) | 1968-03-06 |
| IL23589A (en) | 1969-04-30 |
| FR1457319A (fr) | 1966-11-04 |
| DE1545898C3 (de) | 1975-11-06 |
| DK137191B (da) | 1978-01-30 |
| DK137191C (enrdf_load_stackoverflow) | 1978-07-03 |
| DE1545898B2 (de) | 1975-03-13 |
| US3507860A (en) | 1970-04-21 |
| JPS499475B1 (enrdf_load_stackoverflow) | 1974-03-05 |
| NL144281B (nl) | 1974-12-16 |
| BE664646A (enrdf_load_stackoverflow) | 1965-11-29 |
| AT266315B (de) | 1968-11-11 |
| DE1795694A1 (de) | 1974-02-28 |
| NL6506820A (enrdf_load_stackoverflow) | 1965-11-29 |
| DE1545898A1 (de) | 1970-04-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69621649T2 (de) | Verfahren zur herstellung von cefdinir | |
| DE2760156C2 (enrdf_load_stackoverflow) | ||
| DE1445506C3 (de) | Verfahren zur Gewinnung von reinem a-Aminobenzylpenicillin | |
| CH549051A (de) | Verfahren zum reinigen von 7-amino-cephalosporansaeure. | |
| DE60020869T2 (de) | Ein verfahren zur herstellung von hochreinem cefpodoxim-proxetil | |
| DE2431484C2 (de) | Verfahren zur Herstellung von 7 beta- Amino-7 alpha-methoxy-3-cephemestern | |
| DE2356122C2 (de) | N-Chlorbenzoyl-cephalosporin C-Derivate und Verfahren zu ihrer Herstellung | |
| DE1545897A1 (de) | Verfahren zur Acylierung von Verbindungen der Cephalosporinreihe | |
| DE2412598C2 (de) | Verfahren zur Herstellung von 7-Alkoxycephalosporinen bzw. 6-Alkoxypenicillinen | |
| DE60004054T2 (de) | Neue verfahren zur herstellung von 17beta-hydroxy-17alpha-methyl-2-oxa-5alpha-androstane-3-on | |
| DE2841363C2 (enrdf_load_stackoverflow) | ||
| CH658649A5 (de) | (3rs, 4sr)-benzyl-4-(cyanomethyl)-3-(1'-hydroxyaethyl)-2-azetidinon. | |
| DE1950438C3 (de) | Verfahren zur Herstellung kristalliner Natrium- oder Kaliumsalze von alpha-Carboxy benzylpenicillin | |
| AT223327B (de) | Verfahren zur Extraktion von 6-Aminopenicillansäure | |
| CH646977A5 (en) | Process for the preparation of derivatives of beta-lactam antibiotics | |
| DE1293757B (de) | Reines, stabiles Tetracyclin-hexahydrat und Verfahren zu seiner Herstellung | |
| AT375081B (de) | Verfahren zur herstellung von 7-aminocephalosporansaeure und ihren estern | |
| DE2449870C3 (de) | Verfahren zur Herstellung von 6,6'-Dichlor-6,6'-didesoxy-saccharose | |
| DE2264753C3 (de) | Penicillansäureverbindungen und Verfahren zu deren Herstellung | |
| DE1906194C3 (de) | 3-Brommethyl-A2 -cephalosporine und Verfahren zu ihrer Herstellung | |
| DE2429184A1 (de) | Verfahren zur selektiven spaltung der amidsaeuregruppe eines 7-(amidsaeure)cephalosporins oder 6-(amidsaeure)-penicillins sowie dazu geeignete verbindungen | |
| AT380258B (de) | Verfahren zur herstellung von natrium-ampicillin | |
| DE1903388C3 (de) | Verfahren zur Herstellung des Natriumsalzes von Ampicillin | |
| AT344891B (de) | Verfahren zur herstellung halbsynthetischer cephalosporine oder deren derivaten | |
| AT215598B (de) | Verfahren zur Herstellung neuer Tetracyclinverbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |